Middle managers in higher education hold diverse titles and perform a variety of roles. Women represent a large portion of this midlevel management, but there is limited research exploring their experiences. As a result, little is known about women middle managers' career trajectories and what effect their experiences have on their future career plans. It is not clear if these women want to advance to senior roles or if something is preventing them from doing so. No current qualitative studies address the experiences, aspirations and barriers to advancement for female midlevel managers at private institutions. As a result of thirty interviews conducted with ten participants via Seidman (2006) methodology, ten themes and 43 sub-themes materialized. Five themes and corresponding sub-themes emerged in the areas of (a) career planning, (b) career trajectories, (c) roles of middle manager, (d) expectations, and (e) challenges. Five other themes developed that contribute to the existing literature in the areas (a) support, (b) potential changes, (c) self (personal) barriers, (d) organization structural and cultural barriers, and (e) important leadership qualities. The study confirmed there is a variety of barriers and supports that can affect the career trajectories of women in higher education. More research is needed particularly regarding the themes that emerged. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]